Sex Histories	Sex Histories Archive

New York -- When I was about 35 or 36, I sold all of my possessions and moved to Arizona for three months before returning to New York with my tail between my legs because I couldn't support myself on $5 an hour, the prevailing wage out there then. While I was there, I had no sexual contact with anyone, although I vigorously pursued the visiting son of an elderly neighbor in my apartment complex. When I got back to New York, things picked up considerably.

In a Greenwich Village bar, I met a man named Howard, probably the handsomest man I've ever dated. He was black, tall -- about 6 foot 2 -- and had the striking features of a model. I met him at the moment I was being stood up by another man. Meeting Howard more than mollified my hurt feelings.

View our poll archive

Howard later told me that I was the only person in the bar who interested him, even though I was 12 years older and not nearly as handsome. He said that it was the genuineness of my character, as it showed in my behavior, that interested him. I've gotten more than a few men on the strength of my personality and as I get older I rely on it more.

Dating Howard turned out to be not much fun. He was high-strung and self-centered, so much so that he was seldom able to act like a normal person. He also enjoyed bickering and if he was angry at me for any reason he wouldn't tell me -- he'd just treat me coldly for a week. It quickly became apparent that we couldn't get along.

After about eight dates I realized that I just didn't enjoy his company and I ended the relationship.

Howard has the distinction of being the handsomest man I've ever rejected.

He also has the distinction of being the best-hung man I've ever rejected. The first time we went to bed, he stripped off his clothes to a pair of striped bikini briefs, the bulge of which looked good but not great. He jumped on the bed and started kissing and grinding our bodies together. As we kissed and rubbed, the lump in his briefs grew and grew and grew until the briefs were inadequate to contain it. It popped out, almost nine inches long and thick as a man's wrist.

We had sex only about five times. Three of those times, including the first, he fucked me. The first time, I was surprisingly game. I had had a lover who introduced me to the joys of being fucked by a big dick (though not as big as Howard's) and I figured I could take anything up my ass.

After rubbing and grinding and kissing for a while, I went down on him. He was uncut and there was a bit of cheese odor, but nothing major. Sucking Howard was good but he reacted with more histrionics than I really liked.

The first task was to put the condom on him. His cock was so thick that the condom caused him pain as we gingerly rolled it down his shaft. I couldn't believe that these condoms, which practically fell off my own dick, could barely fit over his.

I lay on my side and gently guided his dick in as much as I could. He had to withdraw once or twice before I could relax enough to really let it in. I had to repeatedly ask him to go slow. Once he was past my sphincter muscle he couldn't contain himself and started ramming it all the way in. I hollered. The feeling was painful but remarkable. He was not only hitting that place deep inside me but I could feel that he was stretching my rectum laterally.

Every time he drove it in, I hollered. After about 10 thrusts, I came, even though I'd given my cock only a few strokes. I think the pressure on my prostate was just too much. Once I'd come I couldn't take his dick at all and I pulled off him. I had to masturbate him to finish him off.

The second time he fucked me was much more successful. He was gentler (at first) and I was more tolerant of the pain. In fact, I discovered that if I didn't holler the pain was more bearable. Instead, I let out a deep groan with every thrust.

He fucked me at on my stomach with my legs spread so that he was getting maximum penetration. The psychological thrill of knowing that I was being so deeply penetrated was immeasurable, but the physical pain still outweighed the physical pleasure.

Howard's dick got very hard when he was excited; it wasn't like some large dicks that never get more than spongy hard. His dick was also completely straight, like a battering ram.

Just at the moment when I couldn't take it any more and I was pushing him off, he came. That wasn't coincidental, since his thrusts became more brutal as he got closer to coming.

The third time he fucked me was the best of all. Like the second time, he fucked me on my stomach, penetrating me deeply. This time I felt pleasure mixed in with the pain. Instead of being just a passive victim, I moved my ass to meet his cock. It was wonderful, After I came, I asked him not to move for a while; I enjoyed the pressure of his weight. I realized then that this was something I could get used to and really like.

Unfortunately, there was not another time.

Author Profile:  Boyd McDonald

Born in 1925 in South Dakota, Boyd McDonald entered Harvard as a high-school dropout after serving in the army in World War II. Jobs with Time, IBM, and several Wall Street firms preceded Boyd's career as a chronicler of gay sex. He was the founder and editor of Straight to Hell (alternatively the Manhattan Review of Cocksucking), and later published a number of anthologies of true sex histories. Boyd died in September 1993, two months after completing his final book, Scum.